Important Organic Conversions

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50 High-Yield Organic Conversions

50 High-Yield Organic Conversions with Reagents and Conditions

1. Methane to Chloromethane

CH4 + Cl2 → CH3Cl + HCl

Chlorine, UV light (Free radical halogenation)

2. Ethane to Ethene

C2H6 → C2H4 + H2

Cr2O3/Al2O3, high temp (Dehydrogenation)

3. Ethene to Ethane

C2H4 + H2 → C2H6

H2, Ni/Pd catalyst, 473 K (Hydrogenation)

4. Ethyne to Ethene

HC≡CH + H2 → CH2=CH2

Lindlar’s catalyst, H2

5. Ethene to 1,2-Dibromoethane

C2H4 + Br2 → BrCH2CH2Br

Br2 in CCl4 (Electrophilic addition)

6. Ethene to Ethanol

C2H4 + H2O → CH3CH2OH

H2SO4, 300°C, 60 atm (Hydration)

7. Ethanol to Ethene

CH3CH2OH → CH2=CH2 + H2O

Conc. H2SO4, 443 K (Dehydration)

8. Ethanol to Ethanal

CH3CH2OH + [O] → CH3CHO + H2O

PCC (Chromium-based mild oxidation)

9. Ethanol to Ethanoic acid

CH3CH2OH + 2[O] → CH3COOH + H2O

KMnO4/H2SO4 (Strong oxidation)

10. Ethanol to Ethyl chloride

CH3CH2OH + HCl → CH3CH2Cl + H2O

ZnCl2 (Lucas reagent), RT

11. Ethanol to Diethyl ether

2CH3CH2OH → CH3CH2OCH2CH3 + H2O

Conc. H2SO4, 413 K

12. Ethanol to Acetylene

CH3CH2OH → BrCH2CH2Br → HC≡CH

Bromination, then alc. KOH (Elimination)

13. Propene to 2-Propanol

CH2=CHCH3 + H2O → CH3CH(OH)CH3

H2SO4 (Markovnikov hydration)

14. Propene to 1-Propanol

CH2=CHCH3 → CH2CH2CH2OH

BH3/THF, then H2O2/NaOH (Hydroboration-oxidation, anti-Markovnikov)

15. Propene to 2-Bromopropane

CH2=CHCH3 + HBr → CH3CHBrCH3

HBr (Electrophilic addition, Markovnikov’s rule)

16. 1-Butyne to trans-2-Butene

CH≡CCH2CH3 + Na/NH3(l) → CH=CHCH2CH3 (Trans)

Na (metal), NH3 (Birch reduction)

17. Benzyl alcohol to Benzaldehyde

C6H5CH2OH + [O] → C6H5CHO + H2O

PCC, CH2Cl2 (Oxidation)

18. Benzyl alcohol to Benzoic acid

C6H5CH2OH + 2[O] → C6H5COOH + H2O

KMnO4, heat

19. Phenol to Salicylic acid

C6H5OH + CO2 + NaOH → C6H4(OH)COONa, then H+ hydrolysis

NaOH, CO2, acidify (Kolbe’s reaction)

20. Ethyl chloride to Ethanol

C2H5Cl + H2O → C2H5OH + HCl

Aqueous KOH, reflux

21. Ethyl chloride to Ethyl cyanide

C2H5Cl + KCN → C2H5CN + KCl

Alcoholic KCN, heat

22. Ethyl chloride to Diethyl ether

2C2H5Cl + 2Na → C2H5OC2H5 + 2NaCl

Dry ether, Na (Wurtz reaction)

23. Methyl bromide to Methylamine

CH3Br + NH3 → CH3NH2 + HBr

NH3 in ethanol, sealed tube

24. Nitrobenzene to Aniline

C6H5NO2 + 3Sn + 6HCl → C6H5NH2 + 3SnCl2 + 2H2O

Sn/HCl or Fe/HCl (Reduction)

25. Benzonitrile to Benzamide

C6H5CN + H2O → C6H5CONH2

Partial hydrolysis (Acid/base)

26. Benzamide to Aniline

C6H5CONH2 + Br2 + 4NaOH → C6H5NH2 + Na2CO3 + 2NaBr + 2H2O

Br2 + NaOH (Hofmann degradation)

27. Acetonitrile to Acetic acid

CH3CN + 2H2O + H+ → CH3COOH + NH4+

Acidic hydrolysis

28. Acetonitrile to Acetamide

CH3CN + H2O → CH3CONH2

Controlled hydrolysis (Partial, base or acid)

29. Acetaldehyde to Ethanol

CH3CHO + 2[H] → CH3CH2OH

NaBH4, LiAlH4 (Reduction)

30. Acetaldehyde to Ethanoic acid

CH3CHO + [O] → CH3COOH

KMnO4 / H2SO4 (Oxidation)

31. Acetone to Isopropanol

CH3COCH3 + 2[H] → CH3CH(OH)CH3

NaBH4 / LiAlH4 (Reduction)

32. Acetic acid to Ethanol

CH3COOH + 4[H] → CH3CH2OH + H2O

LiAlH4 (Reduction)

33. Acetic acid to Ethylamine

CH3COOH → CH3CONH2 → CH3NH2

Convert to amide, then Br2, NaOH (Hofmann rearrangement)

34. Benzoic acid to Benzamide

C6H5COOH + SOCl2 → C6H5COCl;   C6H5COCl + NH3 → C6H5CONH2

SOCl2, NH3

35. Benzaldehyde to Benzoic acid

C6H5CHO + [O] → C6H5COOH

KMnO4 / Tollen’s reagent

36. Benzaldehyde to Benzyl alcohol

C6H5CHO + 2[H] → C6H5CH2OH

NaBH4, LiAlH4 (Reduction)

37. Benzene to Nitrobenzene

C6H6 + HNO3 → C6H5NO2 + H2O

Conc. HNO3, Conc. H2SO4, 333K (Nitration)

38. Benzene to Aniline

C6H6 → C6H5NO2 → C6H5NH2

Nitration, then Sn/HCl (Reduction)

39. Benzene to Chlorobenzene

C6H6 + Cl2 → C6H5Cl + HCl

AlCl3 (Friedel–Crafts chlorination)

40. Benzene to Benzaldehyde

C6H6 + CO + HCl → C6H5CHO

CO/HCl, AlCl3, CuCl (Gattermann–Koch)

41. Benzene to Phenol

C6H6 → C6H5SO3H → C6H5OH

Oleum, then fusion with NaOH, acidification

42. Benzene to Benzoic acid

C6H6 → C6H5COOH

Friedel–Crafts alkylation (MeCl/AlCl3), then KMnO4 oxidation

43. Benzene to Diazonium chloride

C6H6 → C6H5NH2 → C6H5N2+Cl-

Nitration, reduction to aniline, then NaNO2/HCl (0–5°C)

44. Diazonium chloride to Phenol

C6H5N2+Cl- + H2O → C6H5OH + N2 + HCl

Warm water

45. Toluene to Benzoic acid

C6H5CH3 + 2[O] → C6H5COOH + H2O

KMnO4

46. Acetone to Acetophenone

CH3COCH3 + C6H6 → C6H5COCH3

AlCl3 (Friedel–Crafts acylation)

47. Aniline to Phenol

C6H5NH2 + NaNO2 + HCl (0–5°C) → C6H5N2+Cl- → C6H5OH

Diazotization, then hydrolysis

48. Phenol to 2,4,6-Tribromophenol

C6H5OH + 3Br2 → C6H2Br3OH + 3HBr

Br2 (aqueous)

49. Formaldehyde to Methanol

HCHO + 2[H] → CH3OH

NaBH4

50. Ethyne to Ethane

HC≡CH + 2H2 → CH3CH3

H2, Pt catalyst (Complete hydrogenation)

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